PT759917E - Novos inibidores selectivos de neuraminidases virais ou bacterianas - Google Patents

Info

Publication number

PT759917E

PT759917E PT96912404T PT96912404T PT759917E PT 759917 E PT759917 E PT 759917E PT 96912404 T PT96912404 T PT 96912404T PT 96912404 T PT96912404 T PT 96912404T PT 759917 E PT759917 E PT 759917E

Authority

PT

Portugal

Prior art keywords

group

compound according

carbon atoms

groups

alkyl

Prior art date

1995-02-27

Links

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• 230000001580 bacterial effect Effects 0.000 title description 4
• 230000003612 virological effect Effects 0.000 title description 4
• 229940124639 Selective inhibitor Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 659
• -1 antibodies Substances 0.000 claims abstract description 344
• 238000000034 method Methods 0.000 claims abstract description 266
• 108010006232 Neuraminidase Proteins 0.000 claims abstract description 44
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 44
• 102000005348 Neuraminidase Human genes 0.000 claims abstract description 43
• 230000002378 acidificating effect Effects 0.000 claims abstract description 41
• 230000000694 effects Effects 0.000 claims abstract description 20
• 239000000463 material Substances 0.000 claims abstract description 11
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
• 238000003556 assay Methods 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• 229920000642 polymer Polymers 0.000 claims abstract description 8
• 239000003112 inhibitor Substances 0.000 claims abstract description 6
• 230000000890 antigenic effect Effects 0.000 claims abstract 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 126
• 239000000203 mixture Substances 0.000 claims description 121
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 99
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
• 239000002253 acid Substances 0.000 claims description 60
• 150000001413 amino acids Chemical class 0.000 claims description 58
• 125000006239 protecting group Chemical group 0.000 claims description 55
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 54
• 150000002148 esters Chemical class 0.000 claims description 53
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
• 229920001184 polypeptide Polymers 0.000 claims description 48
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 150000001412 amines Chemical class 0.000 claims description 42
• 239000001257 hydrogen Substances 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 38
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 37
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 36
• 229910052717 sulfur Inorganic materials 0.000 claims description 33
• 230000003213 activating effect Effects 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 238000005160 1H NMR spectroscopy Methods 0.000 claims description 29
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 229910052698 phosphorus Inorganic materials 0.000 claims description 27
• 150000001408 amides Chemical class 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 230000002163 immunogen Effects 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 238000002360 preparation method Methods 0.000 claims description 22
• 125000003277 amino group Chemical group 0.000 claims description 21
• 230000015572 biosynthetic process Effects 0.000 claims description 21
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 238000001727 in vivo Methods 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 18
• 238000006073 displacement reaction Methods 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 17
• 125000006413 ring segment Chemical group 0.000 claims description 17
• 230000004913 activation Effects 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000002619 bicyclic group Chemical group 0.000 claims description 16
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 claims description 14
• AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 claims description 14
• AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 claims description 14
• 229910052794 bromium Inorganic materials 0.000 claims description 14
• 125000000539 amino acid group Chemical group 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 150000004820 halides Chemical class 0.000 claims description 13
• 230000007062 hydrolysis Effects 0.000 claims description 13
• 238000006460 hydrolysis reaction Methods 0.000 claims description 13
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• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 11
• 241000712461 unidentified influenza virus Species 0.000 claims description 11
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
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• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 229910052751 metal Inorganic materials 0.000 claims description 9
• 239000002184 metal Substances 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• 239000000741 silica gel Substances 0.000 claims description 7
• 229910002027 silica gel Inorganic materials 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 125000004450 alkenylene group Chemical group 0.000 claims description 6
• 125000004419 alkynylene group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
• 101150065749 Churc1 gene Proteins 0.000 claims description 5
• 102100038239 Protein Churchill Human genes 0.000 claims description 5
• 229910006069 SO3H Inorganic materials 0.000 claims description 5
• 229910052796 boron Inorganic materials 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 150000001735 carboxylic acids Chemical class 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 4
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 4
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002346 iodo group Chemical group I* 0.000 claims description 4
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 238000011321 prophylaxis Methods 0.000 claims description 4
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
• 230000009385 viral infection Effects 0.000 claims description 4
• 108020001305 NR1 subfamily Proteins 0.000 claims description 3
• 229910004727 OSO3H Inorganic materials 0.000 claims description 3
• 229910018828 PO3H2 Inorganic materials 0.000 claims description 3
• 150000004703 alkoxides Chemical class 0.000 claims description 3
• 229910052782 aluminium Inorganic materials 0.000 claims description 3
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
• 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
• 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 229910052711 selenium Inorganic materials 0.000 claims description 3
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• 229910019142 PO4 Inorganic materials 0.000 claims description 2
• 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 2
• 101000996032 Xenopus laevis Nodal homolog Proteins 0.000 claims description 2
• 125000004036 acetal group Chemical group 0.000 claims description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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• 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 claims 2
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• 150000003973 alkyl amines Chemical class 0.000 claims 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
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• 230000008569 process Effects 0.000 description 124
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• 239000004480 active ingredient Substances 0.000 description 32
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
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